


Helping You, Helping Me

by purpleskiesandcherrypies



Series: SPN KINK BINGO 2019 [10]
Category: Supernatural
Genre: F/M, Fingering, Sex, Teasing, bed sharing
Language: English
Status: Completed
Published: 2019-02-20
Updated: 2019-02-20
Packaged: 2019-11-01 07:29:18
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,930
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17862995
Author URL: https://archiveofourown.org/users/purpleskiesandcherrypies/pseuds/purpleskiesandcherrypies
Summary: Growing up with Sammy, you kept him company while your dads were out hunting. You had a huge crush on Dean but you were afraid that he’d only see you as Sammy’s best friend.





	Helping You, Helping Me

Growing up with Sammy, you kept him company while your dads were out hunting. Dean tried his best to keep an eye on both of you but sometimes, even Dean needed some time off and when he was out drinking, which he shouldn’t have been doing, you and Sam would end up reading stories you both made up. Stories full of happiness and quite frankly, different than a life you both lead. Now both your dads were dead and you found yourself in a life of monsters and hunting them, taking over the family business like the Winchesters did. You were still close to Sam. Very much. He was your brother, and Dean… well, that was another story. You had a huge crush on him but you were afraid that he’d only see you as Sammy’s best friend.

Dean walked out of the motel’s office building, frowning before he got into the car and threw the keys to your room to Sam and you could literally see as it slipped out of Sam’s grip and landed on the car’s floor. Sam’s never been good at catching things.

Dean roared up the Impala and Baby purred to life. You always loved the sound and the vibrations underneath your buttocks are sometimes very much welcomed. Especially when Dean’s doing stupid things with his mouth and lips and tongue and it makes you want to squirm or hit him over the head. Then you’d lean back and let the vibration ease your tingling feeling that built up between your thighs. It made it more bearable until you could go and lock yourself up in the bathroom and rub one off.

You trailed behind Dean, walking with your heavy duffel slung over your shoulder as Sam turned the key around in the lock, opening up the door into a dusty, heat filled room. Immediately, Sam turned on the ancient AC and you could hear it rumble to life.

“Dude, there’s only two beds.” Sam said, dropping his duffel at the foot of the bed.

“Dibs on the bed!” You joked, jumping in, landing face first.

“They just have two beds here, alright Sammy?” Dean let out a sigh, planting himself on the couch and you could see the dust flying around him in the wind. “The hell you dibbing on that bed. We have to fight for it. Fair and Square.” Dean growled, his mood not any better, even though he had a driving break now.

“Ok, rock, paper, scissors, it is then.” Sam grinned, winking subtly at you because you both knew what Dean would pick.

It was your turn for the shower because you let them go first, thinking that you’d probably have more time to yourself when they’re all set and done. The only thing you hadn’t calculated was that the motel probably doesn’t have enough warm water for the three of you in one room. Especially not when Sam washed his hair and god, that man can be thorough when it comes to his hair.

After you got out of the shower, Sam was already lying in bed, snoring softly while Dean grunted around, tossing and turning himself on the uncomfortable looking couch.

“You ok?” You asked Dean as you untangled the bathrobe from your hair and let it air dry as you walked over to your bed.

“Huh?” He looked at you, eyes barely open, “yeah, yeah. I’m good. Go to sleep, shortcake.” He said, before turning his back on you.

It was later in the night when you woke up to more of Dean’s grunts. You turned yourself around so you could see him from your bed and witnessed how he flung the pillow across the room as he panted his face into the dirty couch, crying some profanities into the soft surface that muffled his voice.

“Dean.” You said, waiting for him to notice.

“Dean!” A little louder.

“What?” He hissed at you.

“We can trade.” You spoke in a soft voice, not wanting to wake up Sam.

“No, I’m good.”

You were glad that it was dark and Dean couldn’t see you rolling your eyes.

“I saw that.” He said, sitting up on the couch, fingers stroking his ruffled hair.

“You didn’t.” You were smirking.

“Yeah, well, but I know what you’re thinking.”

“Oh yeah? What am I thinking?”

“That I’m stubborn…”

“Yeah, that,” You grinned, “and that you need to keep your voice down because I really want to get some sleep.”

“I try.” He sighed out, rubbing his face with the palm of his hands.

“Really, we could trade.”

“No.”

“Or come here, we share. I’m shortcake, remember? I don’t need that much space.”

“I can’t do that.” Dean shook his head.

“It’s either that, Dean Winchester or I’ll rip you a new hole for not letting me sleep.”

Dean leaned back, contemplating on what to do but when you heard his bare feet scraping along the cheap motel carpet, you smirked because you won that round.

“Move over, shortcake,” Dean’s voice was a whisper now that he was closer and you shuffled on the bed, moving a little so that Dean would fit in with you.

It wasn’t long before you woke up again for the second time with Dean making muffling sounds as he breathed down your neck. You stirred a little and that was when your ass cheeks bumped against something hard.

“Dean?”

“What?” There it was again, the hissing that sounded like a warning, telling you that you should probably go back to sleep.

“You’re fucking poking me, man.” You couldn’t help but grin.

“Ya think?” Dean tried to move away a little but there was just so much space in the bed and if he moved any further, he’d be lying on the floor. “Look, I can’t help it, alright? I’m in bed with a girl who fucking smells like a summer meadow and you barely have clothes on and I’m just not comfortable not being able to do anything about it.”

“Who said you can’t do anything against it?” You tilted your head around to see him cock his eyebrow at you. “We’re both consenting adults, right? I can help you if you help me.”

“What do you mean…” Dean wanted to say more but you arched your back, grounding your ass into his boner, making him bite back a moan that wanted to escape.

You turned around, grinning at him mischievously before hooking your thumbs into the elastic of your panties and sliding them off. Dean couldn’t see it but he felt how your hands were tracing along his legs on their way down.

“What are you doing, shortcake?” He muttered under his breath and you could see that he was doing everything in his power to will himself not to touch you.

“Helping you, so you can help me.” You winked at him, taking his hand and placing his fingers to your lips before you parted them and began to suck them in, hollowing your cheeks. Dean made a sound you’d never heard before. A weird sound of a dying animal that choked to death.

“No, you can’t…” He started to say before he paused to watch two of his digits disappearing into your mouth. You took them out, circling the tip of your tongue at the fingertips as you smiled at him. Dean grit his teeth, his lips quivered, “Fuck it!” He hissed before he took his hand out from your grip and cradled your face and kissed you.

Dean wrapped his hands around you, tracing every inch of your body as his kisses grew more fervent. And when he found your sex and cupped it in his hand, you couldn’t help but moan into his mouth. He swallowed every sound you made.

He parted your folds expertly, his fingers tracing a line from your bud to your entrance and when he pushed in two digits, you moaned into the crook of his neck. You moved your trembling hands down his body, digging into the elastic of his boxers and when you wrapped your hands around his throbbing cock, Dean let out a throaty groan.

“You’re big.” You said before he kissed you again.

Dean broke the kiss, letting his forehead rest on yours. “I’ll be careful if you let me, baby. Will you let me, please say you will.”

He was desperate, you could tell. And you smiled because you were never going to let him hear the end of it even though he’d deny it ‘til the day he died.

When you nodded, you felt him smiling against your cheeks before he kissed his way to your ear, “Turn around,” he said and you did.

Dean got out of the bed and ran across the room to his duffel before returning, his teeth tugging away at the plastic wrapper. He got back in and pulled the blanket on top of both of you before he rolled the condom over his cock. Dean reached over and pulled you into his arms, holding you tight while he guided his cock to your entrance. Slipping in the tip, he moaned and wrapped you up into his arms and held onto you tight as he pushed himself in, sinking into you in a slow pace.

It was obviously too slow to you and you were squirming, needing him to fill you up faster so you ground down, pushing yourself onto his cock as he groaned into the crook of your neck.

“Son of a bitch! What was that?” Dean murmured close to your ear.

“I couldn’t wait.” You tilted your head, grinning as you felt him thrust his hips against your ass.

It was slow and deep and fuck, his dick was hitting you really in all the right places.

Dean mouthed against your hot skin, licking and sucking as he moved his hips and when you felt his digits circling your nub, you moaned out loudly.

“Sshh…” He put the hand of the arm you had your head on your mouth, “we don’t want to wake up, Sammy. Do we, sweetheart?”

Of course you didn’t want to wake up Sammy but damn that hand on your clit and damn that dick in your pussy. You weren’t going to last long.

“Good girl.” He chuckled softly, kissing the delicate spot behind your ear. “Come for me, ok? I can feel you start to squeeze my cock. Come, Y/N.”

His hand was firm around your mouth and you came with trembling feet and shaking hands as you moaned and bit into the palm that was placed on your lips.

“Ah..fuck,” He hissed, nuzzling himself deeper into the crook of your neck as he thrust two more times before he stilled.

You could feel his dick twitching inside of you, pumping out the cum and shooting into the condom.

“Woah..” You said, out of breath as he lazily moved his hips.

“Yeah..” Dean agreed, kissing along your shoulder and neck. “..I think I need to book a room with two beds more often.”

“Are you two done?” A voice from the next bed startled both of you and your heart began to race.

“Sammy?” Dean asked, tilting his head to look into his brothers face.

“Yeah, like I really want to sleep. So I hope you’re done and like, holy shit it took you long enough to make your moves.” Sam turned away, pulling the cover up to his chin. “And Dean?” Sam said again. “Next time, don’t bother with two beds, I’m having my own room.”


End file.
